LOOKING FOR LEGAL WAYS
TO REDUCE TAX?
New tax reduction strategies carefully explained and exhaustively researched every two weeks. Receive breaking news updates on tax law changes. Members only monthly AMA with TOTTB.tax.
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FEATURED CONTENT
A Winner of a Losing Hobby Case
Wolfgang Frederick Kraske, representing himself in Tax Court, pulled off a rare feat. He managed to get two opinions for the price of one in a relatively low stakes case . My friend Lew Taishoff found the regular decision about the $4,574 Section 6662(a) accuracy related penalty to be of great interest . I think the more interesting story is in the memo opinion that covers the tax deficiency of $22,687 for the years 2011 and 2012. It is mostly about Section 183: Activities not engaged in for profit, commonly referred to as the hobby loss rule. Although in this case, the activity does not even seem to get up to the level of a hobby, much less a business conducted for profit. I didn’t dig any deeper into the case, so the story you are getting is what Judge John H. Gale concluded. Kraske might have had something to say if I had interviewed him.
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CURRENT EDITION
Tackling Taxes On an Inherited HSA
The Health Savings Account (HSA) is a first line of defense tax strategy. Contributions are deductible and earnings are tax-free if used for qualified medical expenses. There are numerous features to the HSA that secure maximum tax benefits. Structured properly, an HSA can provide serious tax-free money to beneficiaries as well as the account holder. Before we review the implications of inheriting an HSA, let’s review some of the powerful features an HSA has that increases the value of the account.
Kadau v. Commissioner and the Line Between Effective and Broken Captives
Captive insurance remains one of the most closely examined tax planning strategies in use today, not because it is inherently flawed, but because small missteps can carry outsized consequences. Many taxpayers assume that careful formation and proper documentation are enough to protect the intended tax outcome. A recent Tax Court decision, Kadau v. Commissioner, serves as a reminder that those assumptions deserve closer scrutiny. The court’s analysis did not hinge on whether captive insurance can work, but on how a specific arrangement actually functioned in practice. For tax professionals advising clients who rely on micro-captives, the case raises important questions about where structures tend to break down, why some arrangements attract IRS attention while others do not, and what really separates a defensible captive from one that invites challenge.
Not Every Client Is a Keeper: When Saying Goodbye Protects Your Practice
Bad chemistry with one client can disrupt the flow with everyone. That one client who doesn’t follow your processes and messes up the workflow during tax season. The client who never turns things in on time but then wants results from you immediately when they do. These things affect how you interact and work with your other clients as well. As the firm owner we should do whatever we can to protect good chemistry within our business. As a tax advisor the people we work with become our family. We help them make decisions that impact them and their families. That is why firing clients can be a delicate matter when you are doing the firing.
SIMPLIFIED TAX STRATEGIES &
PRACTICAL IMPLEMENTATION
Think Outside the Tax Box provides tax reduction strategies along with practical
implementation advice in order to reduce your clients’ federal tax bill with ease.
